




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018491/lw2011sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018491/lw2011Isup2.hkl |
CCDC reference: 614614
The title compound was prepared according to the literature method (Jayalakshmi & Gowda, 2004). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Jayalakshmi & Gowda, 2004). Single crystals of the title compound were obtained from a slow evaporation of its ethanolic solution and used for X-ray diffraction studies at room temperature.
The H atom of the NH group was located in a diffrerence map and its position refined. The carbon-bound H atoms were positioned with idealized geometry and refined using a riding model with C—H = 0.93 Å (CH aromatic) or 0.96 Å (CH3). Isotropic displacement parameters for all H atoms were set equal to 1.2Ueq (parent atom).
The stereochemistry of biologically significant alkyl sulfonanilides, particularly in the vicinity of the phenyl–NH portion is of interest as it helps in explaining their biological activity. In the present work, the structure of N-(4-fluorophenyl)-methanesulfonamde (4FPMSA) has been determined (Fig. 1) to explore the substituent effects on the structures of sulphonanilides (Gowda et al., 2007a-c). The substitution of either the fluoro or nitro group at the para position of N- (phenyl)-methanesulfonamde (PMSA),(Klug, 1968) does not change the space group (Gowda et al., 2007a), unlike in the case of meta substitutions in PMSA (Gowda et al., 2007b,c). The bond parameters in PMSA, 4FPMSA and N-(4-nitrophenyl)-methanesulfonamde (4NPMSA)are similar except some changes in the angle, S2N5C6: 120.0 (1)° (PMSA); 120.2 (3)° (4FPMSA) and 128.1 (3)° (4NPMSA), respectively, and in torsional angles, C1—S2—N5—C6, S2—N5—C6—C7, S2—N5—C6—C11: 62.2 (2)°, 75.5 (2)°, -106.6 (2)° (PMSA); -70.7 (4)°, 102.8 (5)°, -78.1 (6)° (4FPMSA) & -67.2 (4)°, -21.5 (6)%, 158.9 (4)° (4NPMSA), respectively. The amide hydrogen sits alone on one side of the plane of the phenyl group, while the whole methanesulfonyl group is on the opposite side of the plane similar to that observed in other alkyl sulfonanilides (Gowda et al., 2007a-c). It is thus available to a receptor molecule during its biological activity. The molecules in the title compound are packed into layer structure (Fig. 2) in the direction of a axis via N—H···O hydrogen bonds(Table 1).
For related literature, see: Gowda et al. (2007a,b,c); Jayalakshmi & Gowda (2004); Klug (1968); Clark & Reid (1995).
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C7H8FNO2S | F(000) = 392 |
Mr = 189.20 | Dx = 1.448 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2243 reflections |
a = 17.272 (3) Å | θ = 3.6–22.0° |
b = 5.059 (1) Å | µ = 0.35 mm−1 |
c = 10.140 (2) Å | T = 293 K |
β = 101.65 (1)° | Plate, colourless |
V = 867.8 (3) Å3 | 0.50 × 0.48 × 0.03 mm |
Z = 4 |
Oxford Diffraction Xcalibur Diffractometer with Sapphire CCD detector | 1757 independent reflections |
Radiation source: fine-focus sealed tube | 1471 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.087 |
Rotation method data acquisition using ω scans | θmax = 26.4°, θmin = 4.1° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2004) | h = −21→21 |
Tmin = 0.852, Tmax = 0.988 | k = −6→6 |
4986 measured reflections | l = −7→12 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.098 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.262 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.20 | w = 1/[σ2(Fo2) + (0.1115P)2 + 1.0115P] where P = (Fo2 + 2Fc2)/3 |
1757 reflections | (Δ/σ)max = 0.001 |
112 parameters | Δρmax = 0.50 e Å−3 |
1 restraint | Δρmin = −0.54 e Å−3 |
C7H8FNO2S | V = 867.8 (3) Å3 |
Mr = 189.20 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.272 (3) Å | µ = 0.35 mm−1 |
b = 5.059 (1) Å | T = 293 K |
c = 10.140 (2) Å | 0.50 × 0.48 × 0.03 mm |
β = 101.65 (1)° |
Oxford Diffraction Xcalibur Diffractometer with Sapphire CCD detector | 1757 independent reflections |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2004) | 1471 reflections with I > 2σ(I) |
Tmin = 0.852, Tmax = 0.988 | Rint = 0.087 |
4986 measured reflections |
R[F2 > 2σ(F2)] = 0.098 | 1 restraint |
wR(F2) = 0.262 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.20 | Δρmax = 0.50 e Å−3 |
1757 reflections | Δρmin = −0.54 e Å−3 |
112 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5825 (4) | 0.0142 (13) | 0.4135 (6) | 0.0720 (16) | |
H1A | 0.5800 | −0.1721 | 0.4302 | 0.086* | |
H1B | 0.5303 | 0.0880 | 0.3990 | 0.086* | |
H1C | 0.6152 | 0.0981 | 0.4898 | 0.086* | |
C6 | 0.7729 (3) | −0.0529 (9) | 0.3838 (5) | 0.0558 (13) | |
C7 | 0.7940 (4) | −0.1872 (12) | 0.5050 (6) | 0.0697 (15) | |
H7 | 0.7612 | −0.3199 | 0.5258 | 0.084* | |
C8 | 0.8630 (4) | −0.1275 (15) | 0.5955 (7) | 0.0833 (19) | |
H8 | 0.8784 | −0.2233 | 0.6748 | 0.100* | |
C9 | 0.9079 (4) | 0.0773 (16) | 0.5645 (8) | 0.084 (2) | |
C10 | 0.8894 (4) | 0.2161 (14) | 0.4461 (8) | 0.0833 (19) | |
H10 | 0.9224 | 0.3510 | 0.4283 | 0.100* | |
C11 | 0.8209 (4) | 0.1538 (12) | 0.3523 (7) | 0.0716 (16) | |
H11 | 0.8073 | 0.2459 | 0.2716 | 0.086* | |
N5 | 0.7032 (3) | −0.1189 (9) | 0.2855 (5) | 0.0605 (12) | |
H5N | 0.683 (3) | −0.271 (6) | 0.294 (6) | 0.073* | |
O3 | 0.6484 (3) | 0.3356 (7) | 0.2684 (4) | 0.0803 (13) | |
O4 | 0.5695 (3) | −0.0318 (8) | 0.1535 (4) | 0.0776 (13) | |
F12 | 0.9756 (3) | 0.1488 (12) | 0.6532 (6) | 0.1259 (18) | |
S2 | 0.62315 (9) | 0.0664 (2) | 0.26953 (12) | 0.0555 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.082 (4) | 0.076 (4) | 0.063 (3) | 0.015 (3) | 0.029 (3) | 0.007 (3) |
C6 | 0.070 (3) | 0.040 (3) | 0.064 (3) | −0.002 (2) | 0.032 (3) | −0.009 (2) |
C7 | 0.079 (4) | 0.061 (4) | 0.073 (4) | 0.000 (3) | 0.026 (3) | 0.004 (3) |
C8 | 0.089 (5) | 0.089 (5) | 0.073 (4) | 0.013 (4) | 0.019 (4) | 0.002 (3) |
C9 | 0.062 (4) | 0.096 (5) | 0.094 (5) | 0.010 (3) | 0.017 (3) | −0.030 (4) |
C10 | 0.068 (4) | 0.077 (4) | 0.113 (5) | −0.011 (3) | 0.036 (4) | −0.018 (4) |
C11 | 0.076 (4) | 0.063 (4) | 0.083 (4) | −0.014 (3) | 0.034 (3) | −0.002 (3) |
N5 | 0.079 (3) | 0.041 (2) | 0.069 (3) | −0.008 (2) | 0.031 (2) | −0.010 (2) |
O3 | 0.107 (3) | 0.0325 (19) | 0.096 (3) | −0.012 (2) | 0.008 (3) | 0.0096 (19) |
O4 | 0.112 (3) | 0.063 (3) | 0.049 (2) | −0.018 (2) | −0.004 (2) | −0.0031 (17) |
F12 | 0.077 (3) | 0.160 (5) | 0.132 (4) | 0.001 (3) | 0.002 (3) | −0.043 (3) |
S2 | 0.0833 (10) | 0.0364 (7) | 0.0463 (7) | −0.0082 (6) | 0.0115 (6) | 0.0026 (5) |
C1—S2 | 1.763 (5) | C8—H8 | 0.9300 |
C1—H1A | 0.9600 | C9—C10 | 1.371 (10) |
C1—H1B | 0.9600 | C9—F12 | 1.372 (8) |
C1—H1C | 0.9600 | C10—C11 | 1.397 (9) |
C6—C7 | 1.387 (8) | C10—H10 | 0.9300 |
C6—C11 | 1.410 (7) | C11—H11 | 0.9300 |
C6—N5 | 1.439 (7) | N5—S2 | 1.651 (5) |
C7—C8 | 1.383 (9) | N5—H5N | 0.859 (10) |
C7—H7 | 0.9300 | O3—S2 | 1.431 (4) |
C8—C9 | 1.368 (10) | O4—S2 | 1.432 (4) |
S2—C1—H1A | 109.5 | C10—C9—F12 | 117.1 (7) |
S2—C1—H1B | 109.5 | C9—C10—C11 | 119.7 (6) |
H1A—C1—H1B | 109.5 | C9—C10—H10 | 120.1 |
S2—C1—H1C | 109.5 | C11—C10—H10 | 120.1 |
H1A—C1—H1C | 109.5 | C10—C11—C6 | 118.0 (6) |
H1B—C1—H1C | 109.5 | C10—C11—H11 | 121.0 |
C7—C6—C11 | 120.2 (6) | C6—C11—H11 | 121.0 |
C7—C6—N5 | 122.3 (5) | C6—N5—S2 | 120.2 (3) |
C11—C6—N5 | 117.6 (5) | C6—N5—H5N | 116 (4) |
C8—C7—C6 | 121.2 (6) | S2—N5—H5N | 100 (4) |
C8—C7—H7 | 119.4 | O3—S2—O4 | 118.2 (3) |
C6—C7—H7 | 119.4 | O3—S2—N5 | 106.9 (3) |
C9—C8—C7 | 117.7 (7) | O4—S2—N5 | 105.9 (3) |
C9—C8—H8 | 121.1 | O3—S2—C1 | 108.8 (3) |
C7—C8—H8 | 121.1 | O4—S2—C1 | 109.2 (3) |
C8—C9—C10 | 123.2 (7) | N5—S2—C1 | 107.4 (3) |
C8—C9—F12 | 119.7 (8) | ||
C11—C6—C7—C8 | −1.8 (9) | C7—C6—C11—C10 | 0.2 (8) |
N5—C6—C7—C8 | 177.3 (5) | N5—C6—C11—C10 | −178.8 (5) |
C6—C7—C8—C9 | 3.1 (9) | C7—C6—N5—S2 | 102.8 (5) |
C7—C8—C9—C10 | −3.1 (10) | C11—C6—N5—S2 | −78.1 (6) |
C7—C8—C9—F12 | 178.0 (5) | C6—N5—S2—O3 | 45.9 (4) |
C8—C9—C10—C11 | 1.6 (10) | C6—N5—S2—O4 | 172.7 (4) |
F12—C9—C10—C11 | −179.4 (5) | C6—N5—S2—C1 | −70.7 (4) |
C9—C10—C11—C6 | −0.1 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O3i | 0.86 (1) | 2.08 (2) | 2.911 (6) | 164 (6) |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C7H8FNO2S |
Mr | 189.20 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 17.272 (3), 5.059 (1), 10.140 (2) |
β (°) | 101.65 (1) |
V (Å3) | 867.8 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.35 |
Crystal size (mm) | 0.50 × 0.48 × 0.03 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Diffractometer with Sapphire CCD detector |
Absorption correction | Analytical (CrysAlis RED; Oxford Diffraction, 2004) |
Tmin, Tmax | 0.852, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4986, 1757, 1471 |
Rint | 0.087 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.098, 0.262, 1.20 |
No. of reflections | 1757 |
No. of parameters | 112 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.50, −0.54 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis CCD, CrysAlis RED (Oxford Diffraction, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O3i | 0.859 (10) | 2.08 (2) | 2.911 (6) | 164 (6) |
Symmetry code: (i) x, y−1, z. |
The stereochemistry of biologically significant alkyl sulfonanilides, particularly in the vicinity of the phenyl–NH portion is of interest as it helps in explaining their biological activity. In the present work, the structure of N-(4-fluorophenyl)-methanesulfonamde (4FPMSA) has been determined (Fig. 1) to explore the substituent effects on the structures of sulphonanilides (Gowda et al., 2007a-c). The substitution of either the fluoro or nitro group at the para position of N- (phenyl)-methanesulfonamde (PMSA),(Klug, 1968) does not change the space group (Gowda et al., 2007a), unlike in the case of meta substitutions in PMSA (Gowda et al., 2007b,c). The bond parameters in PMSA, 4FPMSA and N-(4-nitrophenyl)-methanesulfonamde (4NPMSA)are similar except some changes in the angle, S2N5C6: 120.0 (1)° (PMSA); 120.2 (3)° (4FPMSA) and 128.1 (3)° (4NPMSA), respectively, and in torsional angles, C1—S2—N5—C6, S2—N5—C6—C7, S2—N5—C6—C11: 62.2 (2)°, 75.5 (2)°, -106.6 (2)° (PMSA); -70.7 (4)°, 102.8 (5)°, -78.1 (6)° (4FPMSA) & -67.2 (4)°, -21.5 (6)%, 158.9 (4)° (4NPMSA), respectively. The amide hydrogen sits alone on one side of the plane of the phenyl group, while the whole methanesulfonyl group is on the opposite side of the plane similar to that observed in other alkyl sulfonanilides (Gowda et al., 2007a-c). It is thus available to a receptor molecule during its biological activity. The molecules in the title compound are packed into layer structure (Fig. 2) in the direction of a axis via N—H···O hydrogen bonds(Table 1).